


Skin Deep

by PeachWord



Category: White Collar
Genre: Other, Soul-Searching, Trans Character, Transgender
Language: English
Status: In-Progress
Published: 2016-11-29
Updated: 2017-01-12
Packaged: 2018-09-03 02:03:49
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 4,147
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8692171
Author URL: https://archiveofourown.org/users/PeachWord/pseuds/PeachWord
Summary: Neal has always been called handsome, even beautiful. And while he always knew he possessed dashing looks, he always knew something was missing. (Transgender story)





	1. Chapter 1

**Author's Note:**

  * For [IamNegan](https://archiveofourown.org/gifts?recipient=IamNegan).



> So this is a little different from my other works, but I'm excited to explore different topics. Thank you to IamNegan for creating this idea!

Neal had been called many things in his life.

Con artist.

Thief.

Trouble-maker.

He had also been described a certain way throughout his life.

Blue-eyes.

Handsome.

Pretty.

He didn’t take offense to that last one, perhaps other men would, but not him. Art was pretty, too. The swirls of paint, the strokes of clay. And if he were to be categorized in that way, so be it.  

Though, he never truly accepted these compliments. Did they make him uncomfortable? Yes. Did he know why? No, not really.

He learned early on what to do with these ‘dashing’ looks of his: he worked the system.

A smile here, a seductive wink there.

And why shouldn’t he, he wondered from time to time. They led him to money, treasures, and of course, women.

Neal loved women; the curves of their hips, the roundness of their behinds, the ampleness of their breasts. Just beautiful.

And he found it stranger and stranger, over the years, just how odd it was that he was so mesmerized when in the presence of a naked woman. Most men, he would have to assume, rushed to fulfill the deed, but he drank it in all that beauty.

“I’m flattered that someone as beautiful as you would be attracted to me,” one said as she pierced into his blue eyes.

Neal would laughed it off, replying in a bashful way—the same way he did whenever these compliments were thrown his way.

These types of comments naturally made him look. No, not for hours, or even minutes. It was really just an extra ten seconds here, a second take there.

Was it his dark hair? His eyes? His eyelashes? He would always sigh, walking away from the mirror feeling unfulfilled. The answers had to be there, right?

 

Neal’s phone vibrated against the mahogany stand. Without even prying his eyes open, he reached for it. He sighed as he read the message, it was nothing but an emergency weather update. He nuzzled back into the mattress, hoping sleep would claim him as quickly as it did earlier that night. Though, that had to do with the beautiful brunette adjacent to him. Talia, her name was. An art docent. She breathed deeply, almost gallivanting towards snores, next to him. He listened to the rhythm, even trying to mimic it.

He thought about his day, particularly the operation he had Peter had endured. It was simple enough. Benjamin Towler, a prominent painter in New York’s high society, was believed to be not a painter at all, but rather a brilliant con artist. He allegedly had stolen a book of drawings from an small time artist in Belgium, had allegedly killed him, and was now blowing up the drawings to the size of huge posters, and selling them to the rich for fifty times what they were worth.

“I’ll go in as a waiter,” Neal said, sitting around the conference room.

“No,” Peter said, shaking his head as he looked at the file in front of him.

“Why not? It’s the best way to get in and out of the party. Plus, I can get access to the back rooms, that book of drawings is always close by we determined.”

“Neal,” Diana said, a smirk on her face, “no offense, but you would draw too much attention as a waiter.”

“What does that mean?” Neal asked.

“You’re too good looking. People would pay more attention to you that what is on your serving dish.”

Neal let out a chuckle. “That so not true. You know me, I’ll slip in and out.”

“Diana is right,” Peter said, finally looking up, “you need to be a potential buyer, a society type guy looking to buy millions of dollars worth of his ‘art’.”

“Well if Diana’s logic is true, then won’t people stare at me there too?” Neal countered.

“No, all those rich boys are pretty boys too. You’ll blend right in,” Diana said, the smirk still on her face.

Neal nodded, maintaining that devilish grin on his face. Though, behind that mask, only disappointment bubbled. He was being put back in his corner.

He rolled over onto his side, listening to the deep breathes the lovely woman next to him was making. He glanced at the clock, it was almost 6:30. As quietly as he could, he lifted himself from the mattress and retreated to the bathroom.

He didn’t look in the mirror, he didn’t want to feel so down this early. Everyone saw the beauty in him and he hated that he could not. He understood he had looks that were pleasing, but they were not pleasing to him. There was something missing, he just didn't know what.

As he put his toothbrush back in its holder, he noticed Talia’s tan toiletry bag sitting on the counter. He was always one to pry and so his finger dipped the already open bag wider. There was small compact mirror, a tweezer, a gold tube which he assumed was lipstick, and a travel size black rectangular tube. He grabbed the last item, pulling it out. He twisted the cap off and pulled the wand slowly from its home.

He didn’t even realize he was leaning towards the mirror until the wand was directly underneath his eyelashes. Never had done this before, he was meticulous. He lined the bristles of the mascara wand at the base of his eye and stroked upward. He did this five times until each lash separately glistened in rich noir. A strong calm washed over him—it was like painting.  

He leaned back, taking a long look. His left eye just popped, to him. His lashes could be seen from a distance and he found it enchanting. He proceeded with the other eye and then spent ten minutes just staring.

Beautiful, he thought.


	2. Chapter 2

The mascara incident provoked thoughts within Neal. Thoughts he had never had.

_Am I a man who likes wearing makeup?_

_Can it go farther than that? Do I perhaps like wearing women’s clothing? High heels?_

These thoughts were somewhat scary to him as he had never entered this realm before. However, they were also truly exciting. Other than the fifteen minutes of wearing mascara, he couldn’t remember the last time he felt amped up about his appearance.

One night, he took June’s red jacket up to his room. It was definitely a woman’s jacket, he thought, looking at the pinched waist area. He put it around his body and stood on the tip of his toes, as if wearing high heels. He went to his mirror, and yes, mascara was on his eyes.

He looked in the mirror and a small smile encased his lips.

He washed his face, letting the hardened black flakes melt away, and removed the jacket, intending to get ready for bed.

When he looked in the mirror one last time, the smile was nowhere to be found. The femininity attached to the cloth and mascara left his soul as soon as they were removed and Neal understood this immediately.

What it was, he couldn’t still identify, but he knew it was there.

 

 

Neal sat at his desk, slowly turning the pages of the file in front of him, however he was not really looking at the words. He was looking at the blonde woman, Claire LaFond. She was the most recent victim of a white collar crime and was here giving her statement.

Neal watched, mesmerized actually, as she crossed her legs. The skin had to be smooth. She was petite, yet her limbs were long and graceful. She touched her neck, where a diamond necklace should have been, but had been stolen. Her eyes were green and Neal could see they sparkled, even from all those feet away.

“Caffrey’s on the prowl,” Jones said, chuckling.

Neal snapped out of his daze. “What do you mean?”

“Don’t hide it Caffrey. All you’ve been doing the last ten minutes is stare at the blonde up there.”

Neal himself chuckled. “I think she’s married.”

“Alright, at least I know you have some kind of moral.”

Neal smirked, but his chest felt hot and constricted. “Where’s the phone records?” he asked, looking down at the file.

“Lacey is making copies,” Diana said, referring to the FBI’s newest intern.

Neal nodded. “Going to grab a soda, anyone want anything?”

Jones waved him off as he picked up the phone. Diana shook her head.

Neal barely made it to the bathroom. When he saw he was alone, he locked the door. Hot tears leaked out of out of his eyes and he couldn’t explain them. Matter didn’t help when he caught a glimpse of himself in the mirror. “What is wrong with me?” he whispered to no one.

 

 

 

Lacey shuffled the massive amount of files in her hands. It was a miracle she didn’t drop them as she leaned to her right and tried to press the elevator button.

“Woah,” Neal said, grabbing half of the ones on top. “You’re going to hurt someone with those.”

“Yea, myself,” she said. “Thanks.”

Neal smiled small and nodded. Lacey noticed immediately it was forced. She had seen this man around the office, it was hard not to. He was breathtakingly attractive. She also noticed there was no ego behind it, like he wasn’t one of those men that knew he was so good looking that he didn’t have to do anything for anyone.

“You’d think such as nice fancy building would have a fast moving elevator,” she huffed.

“Yea, the government really allocates it funds well,” he said.

She let out a polite laugh. “I’m Lacey.”

“Neal.” Lacey nodded once. Neal studied the woman next to him. She was average height and build, bold hipster glasses adorned her face. She appeared irritated, but he could tell this was not her normal demeanor.

“God dammit,” she said, hitting the button again. “If I don’t get these down to homicide, they’ll make me stay here all night as punishment. My girlfriend is going to be so pissed if I’m not home by 8.”

“I could take them there for you,” Neal said.

“Oh, I couldn’t ask you to do that.”

“You didn’t.”

She grinned. “That is true.”

“I’ll just put them on the first desk I see, tell them you’re up in White Collar. They’ll never know.”

Lacey thought about this for a moment. “Okay, but I’ll have to buy you a drink in return.”

Neal thought about the offer, and after the day he had, he couldn’t really think of a good reason to say ‘no’. “Sure.”


	3. Chapter 3

“So,” Lacey said, taking a sip from her beer bottle, “is it true?”

“What?” Neal asked, putting his wine glass back on the counter.

Lacey smiled, “Did you really steal that Siberian ruby from the Princess’ safe?”

He chuckled and took a sip of his drink. “Geez, Lacy. We just met. Can’t we wait a little longer? Keep the mystery alive?”

Lacy smiled and nodded. “Fair enough.”

The two continued to drink slowly, but for a while, there wasn’t much conversation, and for some reason, it wasn’t awkward. Lacey studied Neal a little more closely—its what she was interested in doing after she was done with college after all—interrogation.

She had heard many things about Neal Caffrey. Infamous con man. She observed his cheerful demeanor around the office, his ability to melt into any situation, and it was truly fascinating. But today, right in front of her, he seemed out of place, but he was doing an excellent job of hiding it.

“You ever get the feeling you’re not who you think you are?” Neal asked.

Lacey chugged the rest of her ale. “Not sure what you mean.”

“I know that’s a strange question, especially coming from someone like me, someone who pretends to be different people all the time . . . but I was wondering you ever felt like you were walking around in someone else’s skin?”

“Actually,” she said, clearing her throat, “yes.”

Neal’s eyes lit up. It was brief, like a flash of lighting. “Really?”

She nodded. “I grew up in a religious household, you know that story, small town, big church. Anyways, I was never attracted to men. And growing up, I had to pretend I was. I had to go to the prom, both of them, with a boy, I had to go on dates. I mean no one made me, but I had to pretend to be someone else until I came to New York.”

Neal nodded. “What about . . . do you ever go back home?”

“Yes,” Lacey said, “and I don’t hide the fact that I’m attracted to women, or that I have a girlfriend. And to be honest, its liberating to go back there and show them who I am. I’m not ashamed.”

“Wow, Lacey, that’s great.”

“Why do you ask this question, Neal?”

He shrugged, swirling the little wine left his glass around.

“You thinking about changing teams?” she asked, a smirk on her face.

“What? Oh, no, nothing like that.”

“Well then what? Something is bothering you, I can see it in those magnificent eyes of yours.”

And that’s the remark that made him spill. It was always about the eyes. “I don’t feel comfortable with who I am.”

She raised her brow. “You?”

“As a man.”

Lacey’s features relaxed. “Oh, well—”

“I mean, this isn’t recent. I’ve always felt disassociated in a way. I was never into sports growing up. I know that’s not an indicator, but, I never felt a strong alliance with being a male, and I never thought about wanting to be a female, I guess I was just gender neutral really. But then . . . I did think about what it would be like to be a woman . . . and now I can’t stop.”

Lacey handed Neal her napkin. He dabbed underneath his eyes and sniffled. “This is a lot—”

“I know, I’m sorry. I didn’t mean to—”

“No, I’m glad you told me, I meant it’s a lot to deal with yourself.”

Neal chuckled and sniffled again. “Sometimes its easier to talk to a stranger than to your best friend.”

Lacey nodded. “Well, you can talk to me about this, Neal, really. But . . . I know someone else who you could talk to about this if you want.”

“Who?”

“Rachel, my girlfriend. She transitioned two years ago.”

Neal’s eyes sparked again. “Really?”

Lacey nodded. “I’m not saying you have to transition, but she could definitely be someone to ask questions if you’re thinking about it. And you can totally talk to me, as someone who has been there for her. She went through some tough times after she transitioned.”

“Were you with her before she transitioned?”

Lacey shook her head. “No, she had transitioned about six months before we met.”

"Could you tell, that she used to be a man?" he asked. 

"No, I couldn't."

"How did . . . when did she tell you?"

"Very early on, before things got serious. It was a little tough to deal with, honestly, not because I don't accept it, but because I didn't expect it. But she's so amazing, as a person, and that's what I care about."

“I can’t believe this,” Neal said, “what are the odds of meeting you and having this conversation?”

Lacey winked. “Smaller than you think. Should we get another round?”


	4. Chapter 4

**Notes for the Chapter:**

> This is for IamNegan. He is in the hospital tonight. Please pray for him. This chapter and the following ones are for him when he gets back!

Neal through text, agreed to meet Rachel at Crowley, a bar on 81st street.

He ordered a red wine, and as he waited in the corner table, he found himself even more nervous that before. He took out his iPhone and clicked on the camera. He checked his mascara and when everything looked fine, he applied some chapstick.

“Neal?”

He looked up. Before him was a tall woman, around 5’10. She had a slender build, green eyes, and bright fuscia on her lips. A tight garnet dress shaped her hourglass figure. Neal stood. “Rachel. Nice to meet you.”

Rachel smiled.

The two sat. Rachel ordered a dirty martini.

As they waited, they made small chit-chat. Neal studied the woman before him. Her porcelain skin, her elegant posture, the long stands of her red hair. Even Lacey had not of told him, he would have never known.

“Trying to see if I pass?” she asked.

Neal could feel his cheek burning. “Sorry.”

“Oh, honey,” she said, taking a sip, “please. I know I look damn good. I’d look too.”

Neal laughed, thankful she was the joking type. He was immediately attracted to her confidence. “I admire your confidence.”

“I have to be,” she said a little more quietly.

Neal nodded, understanding. In his own line of work, he had to believe he was who he said he was—he had so everyone else would as well.

“When did you know you wanted to . . .”

“Transition?” she asked.

Neal nodded.

“A long time. Ever since I was little. I’m 25 now. I’ve been saving money ever since I was 14 to get the surgery.”

“How . . . how did you know though?”

Rachel shifted in her seat. “I never felt comfortable as a boy. Ever. It was awful, actually. You ever put on an outfit, say in a dressing room, and it’s too small? Can’t even get the pants to zip?”

“Yes.”

“Well imagine having to walk around in those pants, two sizes too small, every day. That’s what it was like for me walking around as a boy.”

Neal licked his lips. “I haven’t felt like that until recently. And when you put it the way you have, it makes me wonder. Shouldn’t I have felt like that?”

Rachel ran her fingers through her hair. “I can’t tell you what’s right, Neal. Some people just figure it out like that,” she said, snapping her fingers. “Others take a little more time to reach that point.”

“I’m not confused,” he said. “For so many years, I’ve had to con people. I’m sure Lacey told you a little bit about my past.”

Rachel smiled. “Sounds like you had fun.”

Neal chuckled. “I did. I most certainly did. But that’s just it. I’ve had to pretend I was someone else, actually, I had to pretend I was a lot of different people. I was so good at it that I had trouble turning it off. I’m just realizing that I never really got to figure myself out.”

Rachel nodded. “That doesn’t surprise me what you’re saying. And you’ve been figuring out yourself since you joined the FBI?”

“Yes. It’s become more and more apparent to me, and I just can’t fight it. I’m a little, not freaked out, because I know this is what I want, but I’m surprised—in a good way.”

“Well, I’m here for you, with any questions you need. It can be tough, I’m not going to lie. You need to have good people around you for support.”

Neal nodded. “Can you tell me the ways it was tough for you?”

“Before I got my surgeries, I was taking estrogen. It took a while for the hair on my face to stop growing, I had to pack on the makeup—but it was obvious I was a man wearing women’s clothing. I got looks, sneers, even in a place as open as New York. People would call me names. I had to get off social media people the people back home in Tulsa were ruthless.”

“I’m sorry,” Neal said.

Rachel smiled. “Don’t be. It made me fight even harder.”

Neal smiled back. He was grateful to have made such a friend. He had a long road in front of him. Now that he knew what road he wanted to take, he needed to make sure Peter, and especially Mozzie, were willing to go along for the ride. 


	5. Chapter 5

**Notes for the Chapter:**

> Hello all,
> 
>  
> 
> I want to apologize for not updating. I have received several, wonderful messages complimenting the story and wanting to know when there will be an update. 
> 
> I originally wrote this story for IamNeegan. I asked him if he would like for me to write him anything, any story line, and he requested this. As some may or may not know, I also wrote my previous story "Raindrops from the Angel's Tears" for him as well. Unfortunately, IamNeegan passed away after a long battle with cancer. I felt I was writing this story for him, and after I learned of his passing, I stopped. However, I have received such a wonderful response from readers to continue, and so in IamNeegan's honor, I will continue to do so. 
> 
>    
> Thanks for your patience, and enjoy!

Peter knocked on the door. _Bam! Bam! Bam!_

“Neal?”

No response.

He entered. The apartment was unquestionably still. The bed was made, the table was spotless. He looked down at his phone. Neal was here, his anklet said so. He looked up and glanced again. The bathroom door was closed.

“Neal?” This time, his voice was softer.

“Peter?”

He scrunched the features of his face together. He knew that tone.

“Are you okay, Neal?”

“Be out in a minute.”

The faucet turned on, the cabinet opened and closed.

“Hey,” Neal said, exiting.

His face was wet, presumably from the fresh wash, but Peter knew the difference between salt water and fresh.

“Please talk to me, Neal.”

“I’m fine,” he said, though it was barely above a whisper.

Peter shook his head. “I know you’re not. Something is bothering you. I know it’s not a con you’re running—if it was, you would be walking around with the smug confident grin.”

Neal spread his lips, showing Peter his pearly whites.

“Don’t be smart,” Peter said.

The smile disappeared.

“You barely talk anymore. I thought you were going through a breakup or something, but I don’t think that’s it. In fact, I can’t even remember the last time you had a woman here. And look at how thin you’ve gotten. You’re on the verge of tears right now.”

“Peter, I’m fine,” Neal said, making his way over to his fridge.

“El said I shouldn’t say anything, that whatever is bothering you would either work itself out or that you would come to me when you felt ready. I am worried about you. Even Diana said something.”

Neal chuckled, grabbing a yogurt. He took out a spoon from the drawer and then sat down at his kitchen table. Peter followed. “What did Diana say?”

“She said, and I quote, ‘I know this will sound strange, but I miss Neal’s smartass comments when we’re in the van.’”

Neal nodded, swirling his spoon around the Greek yogurt. The thick paste never touched his lips.

“C’mon, Neal. Something is bothering you.”

He pinched the bridge of his nose. When he released, his eyes were red and he couldn’t stop the tears. “I’m sorry.”

Peter, quite alarmed, grabbed a napkin. “Did something happen?”

“I don’t know.”

“What do you mean? Did someone hurt you or—”

Neal waved the comment off and blew his nose. “No, nothing like that.”

“Then what?”

“I—”

“Don’t tell me it’s nothing, even you can’t play this off as _nothing_.”

He sighed. It was now or later, and he didn’t really think he could do this anymore—it ate away at him, almost literally. “Peter . . . I . . . I want to be a woman.”

A thin smile spread over Peter’s lips. He put his hands up, palms to the ceiling. “Okay, okay. You don’t want to tell me right now. I get it. Though that’s a very good—”

“No. I mean it.”

Peter swallowed. Neal’s face was stone cold; a defense mechanism. “Are you pulling a con? Is this part of some heist, some grand elaborate scheme? You almost got me.”

Neal didn’t say a word. He had prepared for this moment so many times, rehearsed it in his head, thought of responses no matter which way this would go.

“Neal, are you joking?”

He shook his head.

“But . . . I  . . .okay,” Peter said, running his hands flat over the wood. “But you’re a man.”

Neal nodded.

“I’m confused.”

“I know. So am I, believe me.”

“Confused that you might want to be . . .”

“A woman,” Neal said. “You can say it if you want. I’m not confused about that, I’m confused as to why it took me so long to figure that out.”

“Uh-huh,” Peter said. He licked his lips as he peered into Neal. What he was saying just didn’t make sense to him.

“That’s what’s been bothering me. I didn’t know how to tell you. I know you’re shocked.—”

“Yea!” Peter said, standing up. He paced the room. “But you’re a man, always have been. How does that work? I mean?”

Neal sighed and stood up. “I don’t know. I don’t know anything anymore apparently.” The tears were coming again. He brushed his hand over his face, trying to conceal them. He grabbed the yogurt and threw it in the trash, then turned the faucet on to wash the spoon.

Peter heard the soft whimpers as he scrubbed. He walked over to the sink and gently touched Neal’s arm.

The crying man turned around, his face red and blotchy. “Sorry.”

“Stop saying that,” Peter said softly. “I don’t really understand. This is coming out of nowhere for me, okay?”

“Yes, I get that—”

“Let me finish, please. I’m not upset, if that’s what you are thinking, just confused, like I said. But you’re my best friend. We’ll figure this out, or I’ll help you figure it out. Whatever you need.”

Neal grabbed Peter and squeezed. “That’s the best thing you ever said to me.”

Peter laughed, patting him on the back. “Even better than when I told you you were leaving prison?”

Neal laughed and squeezed harder. “Yes.”


End file.
